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What’s your gender? Man
How old are you? 51
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? United States Western
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
What’s your occupation? Real Estate Investor Owner of Business
What’s your current relationship status? Engaged/Married (open)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Love Women, Love Sex, Two Way Entanglement
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 1

Dental Assisting

How long ago did this hookup happen? 3 weeks

What was your relationship status at the time? Engaged/Married (open)

How would you best classify this hookup? Friends-with-benefits

How long did you know the person before this hookup? For more than 3 years

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? Alysa is five foot eight inches tall, long black hair, beautiful brown eyes and is very outgoing. Intelligent and knows what she wants and goes for it. Alysa is 27, and has a wonderful set of hooters. We are casual friends and I know her from my dentist’s office. I have always thought she was attracted, and as a middle aged man I have had a momentary fantasy that we hooked up but that was all. I have been more like a father figure or older brother to her prior to the hook up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in getting a new crown put on to replace a temporary one that had gone over a tooth that had seen too many fillings. Alysa prepped everything and we talked like we always do and as I do in general, I made her laugh a lot. After it was cemented, I told her I would see her later and went and paid, walking out to my car. At my car Alysa was there waiting for me and I asked her what was up. She said she was off now and was needing to talk to me and wanted to know if we could talk. Sure, I said and we agree to meet across the street at smoothie place.

At the smoothie place we each ordered a smoothie and sat down. Alysa opened up to me there about knowing when someone is right for you. I gave her my opinion and asked about age difference. I talked about it and for me I have always felt in terms of a relationship 10 years (after age 40) either way is about the limit. She asked if my wife was still sick (she suffers for ALS) and I said yes, and she then asked how I dwelt with that sexually. I told her I can engage in sex if I find someone but I hadn’t at that point. How long has it been she asked, and I replied 6 years. That amazed her. She then put her drink down, looked at me and her who demeanor changed. Her right hand reached across the table and took my left hand. Alysa then opened up that no man has made her laugh, feel good about herself, and been so open with her like I have been. Still holding my hand, she stood and so did I and she walked out to my car with me holding hands.

At the car she put her arms around my neck, and kissed me. She kissed me passionately and her tongue entered my mouth, connecting with my tongue and I eagerly kissed her back. It had been so long since I had felt the physical touch of a woman, 6 years of sexual tension came pouring out. “Do you have somewhere we can go?” she asked. “I live nearby and my wife is on the coast with her sister at our beach house. “Great!” and we got into my car, leaving her car parked and went to my house.

At my house I parked in the garage, closing the door and then we got out. We went inside the house and as I shut the door, Alysa kissed me again and then asked “How do you really feel about age?” “You’re fine” I told her quickly changing and modifying my position on this.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? We kissed down the hall to the master bedroom where I removed Alysa’s dental shirt, then her bra and revealed those wonderful, firm and large hooters. Her breasts were amazing and being a breast man, I couldn’t wait to suck and rub them. She undid my shirt and removed it and my tee shirt underneath. Alysa now rubbed her boobs against my chest as we kissed and I felt her hand on my belt buckle. By now I was hard and as she undid my belt, then the top button on my pants and then unzipped me, and pulled down my pants and boxers, I stepped out of them.

Alysa now got on her knees and took my dick with one hand, squeezing the base of my shaft as I grew harder. “After six years you need a release before we fuck” she said. She then began to kiss my shaft and worked her way to my dick’s head and sucked on the tip and top of my dick making me go really hard. She did this for a good five minutes, and then began to shove my hard dick deep into her mouth and then almost back out and then back in. In truth, I was fucking her mouth. She would do this for several minutes and then lick my dick’s head and then shove it in her mouth for several minutes of sucking with my dick moving in and out of her mouth.

It felt so good to be with her and I rubbed her head and played with her beautiful hair as I noticed her tits were now hard and large. I felt my dick fill with cum and so did she. She looked up at me as she shoved my dick rapidly inside of her mouth, back and forth. I suddenly could not hold it any longer and I felt my warm stream shoot into her mouth and I felt her swallowing and shoving my dick to the back of her mouth. I came multiple times, moaning loudly in pleasure.

Alysa now smiled and told me to get on the bed. I watch her go to the bathroom, told her where an extra toothbrush was and mouthwash and waited for her to clean up. She came back rather quickly, smiling and said “Now for the real fun. I have wanted to fuck you for 2 years and I think I may be in love with you.” She then laid down by me as I joined her, and we began to kiss and touch.

My hand now enjoyed playing with those wonderful breast, wetting my fingers and playing with her nipples. She played with my balls and my dick, getting me hard over the next 20 minutes. I eventually moved my hand down to her hairless pubic hair area above her vagina, and then played with her pussy lips and her pussy. I used one finger at first, then two and then back to one to make a come here motion that found her g-spot and turned her on. By now Alysa was soaking wet, her ass slowly making circling motions as we continued to kiss and touch.

After forty minutes of foreplay, I was hard again and Alysa was dripping wet and I wanted to fuck t his beautiful woman so much. I began to move which made her move and she got on top of me. She leaned forward and I rubbed the side of her breasts, turning her on more, as she rubbed my hard dick up and down her pussy area without having my dick enter into her vagina. Alysa moaned slightly “Uhm, Uhm, Oh, Uhm” as she rubbed my hard dick on her clit and pussy lips. For five minutes she did this increasing her pace until she screamed out in pure pleasure “OHHHHHHhhhhh!” and I saw her raise her body up and shoot out a stream of her cum.

Alysa fell on my chest and again moved her pussy against my now super hard dick. She spread her legs out and then sat up and when she sat up, my dick slowly entered her vagina, and she drove it completely inside of her. Her eyes went wide and she said “Your big” and at that point I sat up, and we began to make love. We went slow at first, kissing and looking at each other’s eyes, our matching brown eyes penetrating our souls as my penis was penetrating Alysa physically. Back and forth we rocked, until I started to thrust inside of her. For twenty minutes we kept this up, alternating our pace so neither would come, enjoying making love, fucking each other.

After twenty minutes Alysa picked up the pace and began for the next ten minutes to really begin to drive my dick deep inside of her. She began to moan softly saying “Oh yeah” and “Love it” and “Love you.” I replied finally “Love you too” and at that point Alysa went wild. Her body slammed into mine and my dick now went completely in and out rapidly as she thrust. I felt my cum enter my dick again and so did Alysa since my dick swells and gets even harder as it prepares to ejaculate. “Oh yes, Oh go!” Alysa said and I now took over the thrusting in and out. Suddenly Alysa screamed out multiple times, pulling me close to her , kissing me neck as she squeezed my body tightly. Spasms of orgasms were radiating out from her vagina through her body and she was a wonderful shade of red on her upper torso. I exploded inside of her as I completed a deep thrust into her vagina, feeling my cum stream shot out of my dick. Damn this felt so good. Alysa moaned as I came in her, over and and over,, she began to squeeze my dick, milking it with her vagina to get every drop out.

We collapsed on the bed, my dick still in her vagina, and just smiled and starred at each other. “So is 27 too young for you?” “Hell no” I replied, drawing her near me as she kept squeezing my dick with her vagina. We then talked, and opened up and she wanted to know if I was willing to engage in an affair with her. I told her I was torn. I loved my wife but I need love, affection and companionship. Alysa then said “Let me give that to you. No commitments, no promises, we’ll be lovers and just see where we go.” “Friends with benefits” to use that old adage and Alysa said “Really good friends with lots of sex benefits I say.” With that we started to kiss and touch, and squeeze and feel again. It felt so damn good to feel wanted, to have sex and be with a woman again. We made love two more times in the bed, and then I made a lunch after which we showered and had sex in the shower. Alysa spent the night and we made love two more times and then she made love to me I would say two more times that night. I was a spent man by the end. The next morning I went to my business I own and run, she went to work. We meant up again that night and many nights since, sometimes at my home and often at her townhome.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I have no expectations. I am a man with a wife dying from ALS and will pass rather soon. I have not had sex or affection for over 6 years now, and this hookup showed me that it was possible. I was torn after Alysa left. My wife had told me that I was free to get laid when I needed too, but I hadn’t done it. I really like Alysa, loved our sex and love her friendship and companionship. I won’t be ready for a marriage relationship after my wife passes in the next couple of months but I do totally enjoy being sexually active with Alysa. I told her this and she is fine with it. I am safe for her, and she likes me a lot. We’ll see where it goes after I get through the death of my wife.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Attraction to partner(s), Emotional intimacy, closeness, connection, I was feeling lonely

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? My counselor. Just worked through with me why I think it happened, if I wanted it to happen, how not to have guilt in my situation and to enjoy it.

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? A little bit

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Made me feel alive, and showed me I could still be in a sexual relationship with another and it was fine in my circumstance to find someone to enjoy this with.

What was the WORST thing about this hookup? Touched on it. Feeling I betrayed my wife. I have told her and she communicated it was about time and she was happy since she thought it was a sign I would continue to have my life after ours was over.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I am not one to just walk out and have sex. I have to have an emotional connection to the person and I realized that. I don’t know if I will ever marry again, but I know that I can engage in sex again but that I will do it only with someone I am in a relationship with. IF Alysa had done a one night stand, I would still have done it, but after that, no.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? Nope

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Sex is something we each need, biologically but as I have aged, sex to me is a sign of commitment now. Gone are the days of just getting laid to get laid, I want the closeness and tenderness of a relationship that goes with a very, VERY active sex life. They go together like a hand and a glove.

What do you think about the Casual Sex Project? Interesting

You have a hookup story to share? Submit it here!

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